Small world. I’m as far south as you can go on the mainland, and head to The Keys most every weekend. Gilbert’s, to around Hog’s Heaven, or Islamorada Fish Company / Morada Bay area, usually. Occasionally further, like when ‘Irma’ came to town. I also have 3 H9’s on the ‘board, under MIDI control.
You can mine MIDI to great depths, or keep it simple. What are you picturing? Maybe preset control switching only, with all the MIDI-capable devices? External loop switching, over the non-MIDI drive / distortion pedals? Individual parameter control, continuously variable, under an expression pedal sweep? Your answers will help to narrow down the recommendations
There are a ton of options out there now – simple to complex; relatively cheap to expensive. I’d suggest a relatively simple approach to start, and a device with the capabilities to expand as your MIDI knowledge does. And I know what you mean about the venue space, so compact is a priority.
Nice “second” ‘board. But hey, your ‘baby girl’ is always going to be your baby girl. I can’t really speak to your drive / distortion choices, from personal experience. The Keeley has no pedal match. I will say that a good analog or two makes perfect sense in this local market. I drifted away from being a real purist, as digital distortion is getting so much better now (for my purposes).
But with 3 H9’s … you can cover most any sound or configuration that you can dream up. Under MIDI control, the sky is the limit. I run a small rack, big ‘board, stereo amps / FRFR, complex control, and I lug around an FCB-1010 alongside the pedalboard. Not something I’d push on anyone else, but it works for me.